Pyridine → HCID 66657067, compound

HRID 661587Notes

Reaction equation

O[C:2]1[O:3][C:4]2[C:9]([C:10](=[O:19])[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH3:20].N1C=CC=CC=1.[C:27]([O:30]C(=O)C)(=[O:29])[CH3:28]>>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[C:10](=[O:19])[C:9]3[C:4](=[C:5]([CH3:20])[C:6]([O:30][C:27](=[O:29])[CH3:28])=[CH:7][CH:8]=3)[O:3][CH:2]=2)=[CH:13][CH:14]=1

Participants

Reactant 3

HCID 1049Pyridine

HCID 7918Acetic Anhydride

HCID 178423898HCID 178423898, compound

Product 1

HCID 66657067HCID 66657067, compound

Procedure

Hydroxy-3-(4-hydroxy-phenyl)-8-methyl-chromen-4-one (35.18 g) were combined into a round bottom flask (1 L). Pyridine (38 ml, 2 equivalents) and acetic anhydride (576 ml, 47 equivalents) were added to the round bottom flask while stirring at room temperature. The reaction was monitored by HPLC and was completed instantaneously. There was a change in colour observed, the reaction mixture was dark brown initially and went bright orange with tan brown floccular particles upon stirring. The reaction mixture was poured into chilled, distilled H2O (4 L) and was left stirring at room temperature for 30 minutes. An off-white solid was collected by suction filtration. 1HNMR of the solid in d-CDCl3 indicated it was Acetic acid 3-(4-hydroxy-phenyl)-8-methyl-4-oxo-4H-chromen-7-yl ester with >95% purity The solid was dried on a freeze dryer for 24 hours. When dry, the solid was weighed (31.80 g, 69%).

Workup

stirringupon stirring
additionThe reaction mixture was poured
temperatureinto chilled
distillationdistilled H2O (4 L)
waitwas left
stirringstirring at room temperature for 30 minutes
filtrationAn off-white solid was collected by suction filtration
customwas dried on a freeze dryer for 24 hours
customWhen dry

Sources & evidence

ORD record: ord-2d16066bf24c49028babce777cdd79c8
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084628B2

Reaction notes

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